Nu-(beta-omicron-dialkyldithiophosphoryl)-arylsulfonamides



United States Patent F 3,205,253 E N-(BETA-0-DIALKYLDITHIOPHOSPHORYL)-ARYL- SULFONAMIDES Llewellyn W.Faucher, Lafayette, Calif., and Chester L. Dewald, Houston, Tex.,assignors to Staufier Chemical Company, New York, N.Y., a corporation ofDelaware No Drawing. Filed May 28, 1963, Ser. No. 283,709 11' Claims.(Cl. 260-461) This application is a continuation-in-part of US. Ser. No.106,448, filed May 1, 1961, which is now abandoned.

This invention relates to certain new and novel chemical compounds andthe use of such compounds as selective herbicides. I

More specifically, the invention relates to compounds of the formula:

Aryl SOzNHCHgCHzSP wherein R and R are lower alkyl radicals. The aryl,group in the compounds of the present invention may be either a phenylgroup or a substituted phenyl group.

tion:

Aryl SOzNHCHgCHgCl NaSP- OR, (K01) (NH4CI) Aryl somnomoms NaOl Thesecompounds are prepared by the following reac-" The followingnon-limiting examples illustrate the 1 I preparation of this class ofcompounds:

Example 1.N-'(beta-QO-diethyldithibphosphorylethyl)- benzene sulfonamideA mixture of 116 g., 0.53 M) ofN (beta-chloroethyl)- benzenesulfonamide, 162.4 g. (0.8 M) of ammoniumdiethyldithiophosphate and 250ml. of methyl ethyl ketone was stirred and refluxed for four hours. Thesolvent was removed on a steam bath with an air jet, and the residuetaken up in ethyl ether and washed three times with 3,205,253 PatentedSept. 7, 1965 Analysis 4 Sultur, Nitrogen, Phosphorus, percent percentpercent Theory 26. 00 a. 79 s. 39 Found 25. 69 3.88 7. 69

Example 2 .-N-( beta-0, -diisopr0py ldith iophosph oryl benzenesulfonamide By an analogous, procedure as for Example 1, a mixtureof13.2 g. (0.06 M) of N-(beta-chloroethyl)- benzenesulfonamide, 25.2 g.(0.1 M) of potassium-diisopropyl dithiophosphate and 100 ml. of methylethyl ketone yielded after a four hour reflux period, 20.8 g. (88% oftheory) of viscous product. n =1.5428.

Analysis Sulfur Nitrogen, Phosphorus,

percent percent percent By analogous procedures the following additionalcornpounds were prepared:

Aryl

Phenyl" p-Toluyl. do

'p ChlorophenyL 3,4-ddichlorophenyl "The compounds of thepres'ent'finvention are excellerit tion are used as pie-emergenceherbicides. I

In making the. tests for 'preemergence application, seeds of the testweed species are planted in individual rows one-half inch deep in SantaCruz sandy loam soil contained in 8" x 12' metal flats. Enough seeds areplanted to give about 30 to 50 plants of each weed species in each flat.The flats are watered after planting and the following day each flat issprayed at a rate of 5 pounds of the compound under test in gallons ofsolution per acre. The spraying is conducted as the flat is carried by amoving belt under a sprayer to simulate field spraying conditions. Twoweeks later the degree of weed control is determined" by comparing theamount of germination and growth of each weed in the treated flats withthe weeds in several untreated control flats.

The following chart shows the results of such tests.

Foxtail Annual. Crab grassv Nut grass Bluegrass Compound Ge Gr Ge Gr GeGr Ge Gr Percent Percent 100 511Dll severe effects, 10=normal),m-Iualformation, ch-chlorosis.

Compounds and 16 were tested'slightly difierently. In these tests, seedsof Foxtail, Annua-l' bluegrass, Water grass, and red-root pigweed wereplanted in individual rows one-half inch deep in Santa Cruz sandy loamsoil contained in compressed paper flats 8%" X 6 /2 which are 2%" deep.Enough seeds are plantedto give about thirty to fifty plants of eachweed species in each flat. The flats are watered after planting and thefollowing day .each flat is sprayed at a rate of 20 pounds of the com.-pound under test in 80 gallons of solution per acre. A No. 152 DeVilbiss atomizer is used to spray the solution on the soil surface. Twoweeks later the degree of weed control is determined by comparing theamount of ger- 2. A compound of the formula": v

nsomuomoulsr mination and growth of each weed in the treated flats withg the weeds in several control flats. @SO NHCH CH SPW G ll The resultsof these tests are asfollows:

Foxtail Annual Water grass Pigweed Bluegrass Compound Ge Gr Ge Gr Ge G'rGe Gr Percent Percent Percent Percent 0 .4 0 20- 2 0 5 20 2. 50 5 20 2Legends: Ge-germination, Gr-growth (on a 0 to 10 seale;.0=death or verysevere efiect, 10 =norma1), b-burn, d-desiccatlon.

Compounds 17 through 20 were tested in the same 4. A compound of theformula: manner as were compounds 15 and 16. The test rate, S CHhowever, was 2 lbs./ acre and the weed species tested were I 3 crabgrass, foxtail and water grass. The results were asQSOZNHCHICHZSP(OOHOH3)3 follows: 5. A compound of the formula:

01 Crab grass Foxtall Water grass 8 CH Compound S OzNHCHzCHzS P(OCH-CH3) 7 Ge Gr Ge Gr Ge Gr 1 Percent Percent Percent 8 g 8 6. Acompound of the formula: 10o "i 100 100 f 100 3 100 5 100 a g@somncmomsmoourm Legends: Ge -germination, Gr-growth (on a rating systemof 0 to 10; 0=death or very severe efiects, 10 =n0rmal). 7; A compound.the formula:

We claim: S 1. A compound of the formula: T

S OgNHCHzCHzS P 0 03117):

v s onl 01 I -SOzNHOH CHzS P\ 8. A compound of the formula:

0R2 g/O-Cflfh- -somuonzonlsr wherein R and R are lower alkyl and X 1sselected from O-CHCI-Ia the group consistmg of hydrogen, chlorme, loweralkyl and nitro. o H;

9. A compound of the formula:

S OgNHCHaCHzS P 10. A compound of the formula:

A compound of the formula:

OCH

OCHCH:

OCH

6 References Cited by the Examiner UNITED STATES PATENTS 3/55 Cupery eta1. 712.6 5/56 Toornman 71--2.6 8/57 Metivier 260-461 11/58 Sehrader260-461 12/58 Baker et a1. 260-461 X 7/ 59 Schegk et a1. 260-461 10/61Berkelhammer 260461 FOREIGN PATENTS 4/55 Ger-many.

CHARLES B. PARKER, Primary Examiner.

5 IRVING MARCUS, Examiner.

1. A COMPOUND OF THE FORMULA: